


Calling In a Favor

by thatwriterlady



Series: 25 Days of the Holiday Season [23]
Category: Supernatural
Genre: Anna Milton Comes From Money, Anna Milton Likes Charlie Bradbury, Anna's Father Is A Douche, Architect Dean Winchester, Best Friends, Billionaire Dean Winchester, Castiel Likes Dean Winchester, Charlie Bradbury likes Anna Milton, Christmas, Christmas Party, Dean Winchester Likes Castiel, F/F, Good Dean Winchester, Irony, M/M, Matchmaker Anna Milton, mansion
Language: English
Status: Completed
Published: 2020-12-23
Updated: 2020-12-23
Packaged: 2021-03-10 23:02:47
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 7,328
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28415085
Author URL: https://archiveofourown.org/users/thatwriterlady/pseuds/thatwriterlady
Summary: Anna Milton is one of seven heirs to Milton Industries, a generational business that has existed for more than a hundred years. It thrives on the suffering of those who don't have the kinds of funds to stand up to them. They take land from people, destroy entire towns to remake them into places that will line their pockets that is, until they came up against Dean Winchester.Dean's a successful businessman in his own right and in just his lifetime he's built an empire of his own, worthy of standing up against the greed of Howard Milton the third. When the yearly Milton Christmas party rolls around Anna begs Dean to attend with her, even though she knows it would infuriate her parents. She lures him in with the offer of introducing him to her brother.It's definitely going to be a party to remember.
Relationships: Castiel/Dean Winchester, Charlie Bradbury/Anna Milton
Series: 25 Days of the Holiday Season [23]
Series URL: https://archiveofourown.org/series/2037259
Comments: 6
Kudos: 88





	Calling In a Favor

**Author's Note:**

> I'm sorry it took so long to get this one put on here. I sort of burned out for a bit. I had this 90% finished but I kept poking at it. It may or may not suck. I'm sorry if it does. Hopefully it doesn't suck too bad. My migraines have been bad lately, so I'm hoping my fuzzy brain isn't screwing up this story and the last few I still need to write. Fingers crossed!

**Dec 23rd:**

**_Calling In a Favor~_ **

“Dean, please, I’m begging you,” Anna pleaded. “I can’t go home single again, I’ll probably choke my mother to death if I have to tell her I’ll be there alone. She 100% will have some guy there under the ruse of having been invited to the party, but really he’s there because she’s trying to set me up. She does it to all of us, but the last guy she tried that with? I ended up decking the bastard because he put his hands on me. Mom was embarrassed that she’d “chosen so poorly”, but had no remorse that she’d chosen anyone in the first place! I am  _ begging  _ you! It’s their annual Christmas party, so no gift exchanging, we’ll do that as a family on the 25th, but this stupid party…”

“Can’t you just  _ not _ attend?” He asked. “You realize I’m gay, right? Won’t they see right through this charade?”

“I don’t care if they do, as long as they do it  _ after _ wards. I just want to survive the party and go home until I’m summoned for actual Christmas.”

“Summoned,” He snorted as he moved his phone to his other ear so he could start loading the dishes into the dishwasher. “Your family is a hoot.”

“You mean nightmare, they’re a nightmare.” She huffed.

“Ok, so let’s say I do this for you. What’s in it for me?”

She was quiet for a few seconds before she started giggling. There was something very mischievous about it. “I’ll introduce you to my brother.”

“Annie, dear, you have  _ six _ of them and the two I’ve already met, I was not impressed with. Mike’s a stuffed shirt and Luke’s an asshole.”

“No, I’m introducing you to my favorite one of all, though don’t let Gabe hear me saying that. Trust me, you’ll like him.” She seemed so smug. It intrigued him.

“Ok, got a picture?”

“Nuh uh, you come with me or I won’t ever introduce you. You’re going to come and meet him in person.”

He sighed and after putting in a soap pod, closed the dishwasher and started it. “Fine, but you better not let your mom start talking about weddings and crap. When are you going to tell her you’re a raging lesbian?”

“I’m not a  _ raging _ one,” She giggled. “I’m the only girl, so broaching the subject...it’s kind of delicate.”

“And yet you say two of your brothers are bi and one is gay. That’s more than half their kids that are queer. They’re not suspicious yet?” He laughed.

“My mother is the epitome of denial,” She replied. “You’ll find that out soon enough. Pick me up at six, the party starts at seven. This Saturday.”

“Fine. How fancy is this thing?”

“This is my family we’re talking about. You know it will be fancy. Put on your nicest suit. It’s bad enough that I have to wear an evening dress. I am  _ not _ happy about it.” She grumbled.

“Good thing I have several tailored suits, all name brands. I’ll charm the socks right off her snobby friends, and that’s if she doesn’t flip because it’s  _ me _ you’re bringing. At least you won’t have to explain Christmas morning why we didn’t work out. You won’t have to suffer until the  _ next _ party she tortures you with.”

“Hush you, she throws another one at New Year’s, but I’m deliberately avoiding that one. I can safely come up with excuses to get out of that one. It’s more for her friends than anything. The Christmas one though is non-negotiable,” She sighed with relief. “Thank you so much for doing this. You’re the best friend a lesbian could ask for.”

“You’re lucky I love you,” He teased. “Fine, I’ll be outside your house at six. Go practice your evasion skills, you’re going to need them to be sharp if you plan to survive this party.”

She laughed but he was right. “Ok, I’m going. I’ll see you Saturday.”

He hung up and sighed heavily. The things he did for his friends…

@@@@@@@@@@@@@@@@@@@@@@

Saturday night Dean pulled up in front of Anna’s house to find her already waiting. Before he could get out and open her door for her she was sliding into the passenger seat. 

“You look amazing, hon,” He told her. It was true, she was a beautiful woman to start with but when she dressed up and did her hair she was stunning. Men everywhere drooled, but they didn’t stand a chance. She touched her perfectly styled hair and smiled.

“I went and got my hair done. If I’d shown up with it hanging down I’d never hear the end of it.” She said with an eye roll.

“Wow, I’m kind of intimidated by your mother. I know you were born into money and you come from a family of socialites, but I grew up poor. I clawed my way up to get where I am today. I’m not refined, she’ll see right through me. I know how much your father hates me, and it’s a miracle that it’s  _ me _ you wanted to escort you tonight. I don’t want your parents angry with you, especially if they realize you’re attending with the man your father sees as his enemy, and that enemy is  _ gay _ .” He worried as he pulled away from the curb. “I just don’t want to cause problems for you.”

“You won’t. Frankly? My goal in life was never to be a snob, nor is it to live up to their high expectations. Who my friends are, I honestly don’t care what their opinions are of them. My mother will see you as new money and while she tends to snub her nose at that, I’m her thirty year old single daughter. At this point I think she’d marry me off to a pauper as long as he put a ring on my finger. It’s my father that I intend to avoid tonight. While they will do  _ anything _ to avoid causing a scene, especially since there will media present, there will be security around, and I wouldn’t put it past my father to have them take you out the back door. In that case you can count on my  _ brothers _ to make a scene. Security puts one hand on you and there will be enough drama to cause a commotion among their friends and business partners to last ten lifetimes. So don’t worry, you’re safe.”

“You really need to tell her you’re gay,” He glanced over at her and frowned. “Maybe tonight’s a good time? Your mother will be surrounded by all of the people that she tries so hard to impress and make jealous, so it’s unlikely that she’ll make a show. Right?”

“I have no idea. I’m so tired of this dance with her though. Maybe you’re right. If not tonight, then maybe at Christmas. I really wish I had a couple of sisters for her to focus on so I could get some peace.” She sighed.

“With half their kids being queer, your sisters would probably be gay too,” He joked. She grinned at him.

“You’re probably right, but at least we’d be miserable together!”

@@@@@@@@@@@@@@@@@@@@@@

It was an hour drive out to the Milton residence and as they pulled up Dean couldn’t help it when his jaw dropped. This was a mansion, like an honest to God  _ mansion _ ! And there was valet parking. How much did her parents spend on these parties? He pulled up in front and after helping Anna out of the car he took the ticket from the valet and offered his date his arm. Anna smiled sweetly and with all of the holiday lights that seemed to light up the very night, there were so many, he could see her perfectly applied makeup, complete with red lipstick. Very festive.

As they passed through the front door and stepped into the grand foyer, his eyes nearly bugged out of his head. Marble floors, chandeliers, mahogany balustrades that lined perfectly polished matching mahogany railings that followed the staircase up to the second landing where they branched off in two different directions. There was a Christmas tree in the corner with so many lights and decorations he honestly couldn’t tell if the tree itself was white or green. It was beautiful either way. There were presents neatly arranged beneath it but he suspected those were empty boxes, just there for show. 

There were more Christmas lights, literally everywhere he looked. Lining the doorways, winding up the railings, there was not a single place his gaze landed that there weren’t crisp, white, holiday lights adorning, save for the party guests. They hadn’t even reached the parlor before there was a server there offering them glasses of champagne. They graciously accepted theirs, but he planned to walk around with his and not really drink it, lest it be replaced. He didn’t want to be forced to spend the night here because he was too buzzed to drive home.

“Wow, this is  _ a lot _ of people,” He knew he was still looking around at the decorations with what appeared to be a look of wonder. What he was really doing was marveling over how high the Milton’s light bill must be, especially during the month of December. A grand?  _ Two _ grand? This was a mansion after all.

“I have no idea who most of them are,” Anna admitted. “But I think most of them are on the chairmen’s committee with my father.” Her father owned less than a sixteenth of Mill Ridge, which was where Dean lived. Milton Industries has their hand in quite a few different businesses, one of which was the largest grocery store chain in the country. Another was real estate. They liked to buy up property, targeting small towns in prime locations, close enough to big cities, yet country enough to appeal to those wealthy city folk looking for a quiet place to live and once every property was in their name they would raize the entire place and build subdivisions. That plan snagged when they got to Mill Ridge. Dean had seen them coming from a million miles away thanks to Anna and he’d called a town hall meeting, letting everyone in town know what was coming. Some people, mostly those with failing businesses or struggling to maintain their properties thought that might be a good idea. Dean offered them protection and the chance to stay in their ancestral homes.

Mill Ridge was a nice place to live. For the most part everyone lived comfortably. Sure it was a small town, barely two thousand people, but the land was extremely valuable, especially for developers. It was nestled in a valley surrounded by three major cities which made it the perfect place to build something entirely new that catered to the Milton Industries . Howard Milton the third, Anna’s despicable father had wanted the entire valley. He had plans for his own town, all centering around Milton owned properties. There would be a Milton’s, their grocery store, a half dozen subdivisions, a medical center supplied by Milton pharmaceuticals and more. The land was so perfect, and Howard, the greedy, greedy man that he was, had sent in his sharks. That was Dean’s hometown. He’d been born and raised in Mill Ridge. It was where he’d begun his architectural firm, and where he was blessed to have it suddenly boom. It was where he’d built his house, his life, and  _ no one _ was going to take that from him, least of all Howard Milton. 

The irony was that Dean had met Anna Milton purely by chance. She’d been at a party thrown by some friends back when they were in college and they’d instantly hit it off. Back then he’d been a simple architecture student, and she’d been in for business management. There hadn’t been any issue with them being friends. He introduced her to all of his queer friends and she found kindred spirits. He was the first person she came out to, and he’d kept her secret. She’d eventually come out to her brothers, but not their parents. Despite the expensive education her parents had paid for, and the degree her father had demanded she get, she hated working for the family business. 

When her father set his sights on Mill Ridge she’d immediately gone to Dean to warn him. She’d spent much time visiting him, had even considered buying a house near him and selling the oversized one her parents had bought her because she much prefered the small town to the big cities. Then she, along with her siblings had been brought into a planning meeting, to review possible locations for new subdivisions. The second she’d seen Mill Ridge on that list her stomach had dropped. Despite her efforts to direct them towards other places, her father had zeroed in on Mill Ridge. She just couldn’t let him destroy such a beautiful place for his own greed.

Because of her warning Dean was able to thwart Howard’s plans. His money didn’t come from generations upon generations of aristocratic wealth but he’d made his own fortune and wasn’t one to give up easily just because someone thought they could bully him. He’d worked hard to build his own business, Howard wouldn’t know hard work if it smacked him in the face. He didn’t understand what it was like to come from nothing and claw his way up, to value every single advancement he made and be truly thankful for all of the good things that happened to help him earn his wealth. Howard just expected it, simply because his last name was Milton. Dean was glad Anna was  _ nothing _ like her father. 

The first big mistake Howard had made was underestimating him. He’d taken Dean for just some country bumpkin, just another of the “little guy” that he railroaded on a regular basis. His second big mistake was assuming that Dean was just another blue collar worker. In his youth he had been, but not anymore. Dean was a shrewd businessman who knew how to build his own wealth. He didn’t depend on others to do it for him, and now he owned the largest architecture firm in the United States. If Howard had just done a little research he’d have known he would never have Mill Ridge.

His refusal to let Howard steal his hometown from him had led to the current stalemate. Milton wanted the land, but the good people of Mill Ridge had sold their properties to Dean, knowing he would protect them and their town. Only one farmer, with a whopping eight acres had been stupid enough to sell to Milton. Howard wasn’t used to being challenged like this, not by someone so much younger, and that didn’t fear him and his power. If he knew his only daughter was friends with Dean he’d most definitely lose his shit. Dean wasn’t stupid, he knew that was why, of all her male friends, Anna had asked  _ him _ to accompany her tonight.

They entered the parlor and could smell pine, or what they could of it with all of the cologne and perfume permeating the air. Anna spotted a friend and dragged Dean over to meet her. The next half hour was spent talking to the woman, until Dean grew bored. He excused himself to wander off and see what else there was to drink. The night was still young and one drink wouldn’t hurt, not if he followed it up with water.

There was a bar and he wove through the crowd to get to it. It was not surprising to find that they were serving top shelf liquor, so after getting the whiskey he’d been after, he decided to look around.

Stepping back into the much less crowded foyer he found himself drawn to the Christmas tree. He’d bought a massive one for his mother’s house that she decorated with all of the ornaments he and his brother had made growing up, but also the ones they bought each year for her since then. The tree was full of them and the little glass balls she loved, and he thought it was much more beautiful than this, and this one was beautiful.

“It’s lovely, is it not?” A deep voice asked from his left. He looked up to see a man standing on the stairs, coming down from the second floor. Upon being acknowledged he came down to the foyer and around the corner of the railing to where Dean was standing.

“It is. I was just thinking about my mother’s tree. This one is nice, beautifully decorated, but I like hers much better. She hangs the ornaments my brother, Sam and I made in school when we were kids, but also all of the ones we’ve gotten her as adults. It’s pretty much as full as this one.” He explained. The man was looking at the tree, perhaps trying to picture the one that stood in Mary Winchester’s living room. 

“It sounds wonderful, much less forced than this one. This is just for decoration, the real one is in the den, though it’s not much different than this. I think it would have been nice to have handmade ornaments.”

Dean studied the man. He looked enough like Anna’s brother Mike to make him think this was one of the Milton brothers. He was gorgeous, with dark hair, blue eyes, and full lips that turned up in a soft smile when he noticed Dean looking at him. He was dressed in a three piece suit that screamed “money!”, but wasn’t so expensive as to say he was like the snob his father was. It felt like it was expected of him to wear an expensive label, so he’d chosen one of the lesser expensive suits they had. It was navy blue and he looked fantastic.

“Are you a Milton?” He asked. The man’s smile widened a bit.

“I am,” He offered his hand. “I’m Castiel, but you can call me Cas.”

Dean shook it, surprised by the firmness of the man’s shake. “Dean. I hear your mother likes to throw these parties several times a year.”

“Yes, unfortunately,” Cas rolled his eyes. “I hate them. Were my presence not mandatory I certainly would  _ not _ be here,” He looked Dean up and down, the lights from the tree making his eyes almost seem like they were glowing. When he met Dean’s gaze there was definite interest in his eyes. Was this the gay brother Anna kept mentioning? “Are you here with someone? I don’t think I’ve seen you here before.”

“I’m here with your sister. She asked for an escort so your mother wouldn’t try to set her up. She hates that.”

Cas laughed, and this time when he smiled it was so wide his gums and teeth were on display. He’d definitely had excellent dental care growing up, and probably very expensive braces at some point since his teeth were perfectly even. It was an odd thing to notice about a person, but Dean was extremely observant.

“Mother doesn’t know yet that she’s a lesbian. She complains all the time that Anna hasn’t found a nice man and settled down yet. The rest of us, we all know and no one else cares that she is. Hell, I’m gay and my brothers Luke and Gabe are bisexual. As long as we’re not bringing men home to meet the family she allows herself to pretend that we’re not. It’s really rather annoying. Our father is the real issue. “No good Milton man is a pansy”,” Cas shook his finger as he mocked his father. “You just need to find the right woman, one with status that will improve the Milton name.” It’s really annoying. My brother Gabe loves irritating him every chance he gets.”

“I suppose I’m lucky then,” Dean said. “My parents never cared that I’m gay. My father has passed away but my mother supports me and loves me unconditionally. Does she want me to find a nice man to settle down with? Absolutely. She tries setting me up from time to time, which is why I agreed to come with Anna tonight. I understand her frustration. My mother isn’t as bad as yours though.” He kept his voice low as a couple walked by, slowing to look at the tree as they passed. Cas was definitely looking at him with interest now. He preened a bit at the attention.

“You’re Dean...Winchester, are you not? Anna speaks very fondly of you. In fact,” Cas moved close enough that Dean could smell his cologne. “She said she wanted to introduce us tonight. She seemed very certain that I would like you. I told her I already did because you put a serious wrench in our father’s plans to take over your town. He has been highly unsuccessful in procuring any properties beyond the one farm he was able to purchase. If I remember correctly, you bought the entire town  _ and _ you have a five hundred acre farm in the middle of the valley? Anna talks about how much she likes visiting, and that you go horse riding. The way she described Mill Ridge, it sounds like a wonderful place to live. Better than this stuffy mansion we grew up in, or the houses our parents bought for each of us. They have no idea but I rented mine out. I have a cozy, two bedroom condo in the heart of the city.”

Dean grinned. Castiel was possibly even more rebellious than his sister. He got why she had wanted to introduce them. “I like you, Cas. Anyone that has morals and strong ethics is good in my book.”

“I have a much stronger moral compass than my father. I do not believe in screwing over the less fortunate. I didn’t  _ ask _ to be born into money, none of us did. We’re all on the committee now, preparing for when he passes the reins, but the second he is dead, we’re changing  _ everything _ . As the oldest, Mike and Luke are his right hand men. He trusts them so much that they’ve seen the will and they know all of the stipulations and exactly what everyone’s inheritance will actually be. They made copies for all of us, and they’ve done so every single time amendments are made to it. The company is massive and we’re all getting a part of it. We plan to try our hardest to correct it all. Father wouldn’t allow that while he is alive but there are ways around the will. Besides, his lawyer? It’s Mike’s wife. She makes the amendments whenever our father issues one. He tried to cut Bart out of the will. As far as he knows, Bart  _ is _ out. Our mother is aware that Nora never took him out. Besides, she’s more concerned with her social status and impressing her equally snobby friends than she is in us, in the company, or even in our father. As long as we don’t shine a negative light on her, she doesn’t care.”

“What if you wanted to get married?” Dean asked. “If she’s so in denial of her children’s orientations, wouldn’t she be upset?” Dean wondered. Cas slipped his hands into the pockets of his pants and shrugged.

“No one has done it yet, so who knows? Mike and Bart are married, Inias is involved with a lovely woman who does  _ not _ come from money, much to my parents’ chagrin, and Gabe, he enjoys having a ménage à trois as often as possible. Father puts a lot of money into covering that up. He expects discretion from all of us but my brother is allergic to the word.”

They quieted as another couple stopped to look at the tree. Once they’ve moved on Cas gave a nod of his head towards a closed door on their right.

“Care to join me in the study? I’m not very interested in parties filled with snobby socialites, unless you are? I don’t want to monopolize your attention.”

“Please, monopolize away,” Dean’s smile was charming and Cas’ gaze zeroed in on it. “I’m only here as a favor to Anna, but she ditched me. I had the feeling she would anyway.”

“She’ll seek you out eventually. Listen for your phone, she’ll text.” Cas opened the door and stepped back so Dean could enter first. He followed him inside and closed it. Dean walked over to the settee across the room. Dark blue, crushed, velvet, it was large enough for two grown men to sit, but they’d be sitting close. Cas joined him and together they sat down.

“So you said you live where? Is it close to here?” Dean asked.

“The house he bought for me is a two minute drive from here, not that they would  _ ever _ visit us in our homes,” Cas sounded irritated. Dean knew it was directed at his selfish parents. He felt even more sorry for the Milton kids. “Being the youngest my mother tried to get me to stay, but I could never live here again, I’d lose my mind. My father is almost never home, but my mother is around, when she’s not at one of her various clubs or gatherings. Then there are staff and other people constantly coming and going. I like quiet, and not having my mother invite herself into my quarters whenever she feels like it. It was awful when I was a child but it’s downright embarrassing as an adult.”

“Dids she catch you doing naughty things?” Dean teased. Cas chuckled and though his cheeks flushed slightly, he held his composure.

“Let’s just say she has a knack for choosing the most inopportune times. I’m much happier living far away. She’ll call me and ask me to come visit or meet her somewhere for brunch. It’s why neither of my parents know I’m not living in the house. I don’t need a six bedroom house, I’m a single man. Perhaps when I have a family of my own, but not yet. Even when that happens I  _ still _ won’t have a house anywhere near here.”

“I have a ranch. Well, it’s a sort of farm and ranch. I breed three different kinds of horses, I have staff that give horse riding lessons, I have a small herd of Longhorn, a dozen alpacas, chickens, ducks, and some other things. Then there’s the crops and the wildflowers. I keep bees. It’s sort of a little bit of everything,” Dean angled his body so he was facing Cas more. “As you may know, I’m an architect, so I designed and built my house. It’s two stories, five bedrooms, three bath, full, finished basement, and twelve rooms in total. At the time I was like “I can have a big house and I can do anything I want in it”. Now that I’m actually living in it I’m realizing just how big it is, and how lonely it can get. I hope to have a family to fill it up with someday. It’s the perfect place to have kids running around.”

“It sounds wonderful,” Cas said. “Everything about it sounds amazing. You see what this house is like. I think my mother would have a heart attack at the thought of owning an alpaca. I’m not even sure she knows what they are, despite having coats made of their wool, but I’m the wild child. If I was told I couldn’t do something, that just made it more appealing. I wasn’t allowed to have pets, so I snuck a cat in and kept it in my quarters for three years before she realized it was there. She was furious, tried to get rid of it but I threatened to tell her friends about her liposuction. They all envy her for her figure. If they knew she didn’t look that way naturally they’d lord it over her forever. So, I got to keep my cat. I still have her, actually. She’s nineteen, frail, but she’s a sweetheart. Spends most of her time sunbathing on the window seat in my living room. I wasn’t allowed to have friends outside of those I went to school with, so I made friends with the children of the staff, with people online, and anyone else that  _ wasn’t _ someone I went to school with. If I knew it would irritate my parents, I did it. Short of drugs, I never did drugs. Well, weed, I did  _ a lot _ of that!”

Dean laughed at that. “So you’re the wild child. Are you much younger than Anna? I know she’s a few years older than I am. She was already on her masters when I was starting my bachelors.”

“She’s a year older than me. My mother says I’m the reason she has to color her hair,” Cas snickered. “I’m asked to come for holidays and a few parties, but otherwise I don’t come here. I’ll have the occasional brunch with my mother. Besides, I embarrass my mother. I drive a ‘77 Oldsmobile, I have no interest in wearing five thousand dollar suits, I like jeans and tee shirts, and I garden. It’s beneath her to do the help’s work. I love that you raise bees. I work with fifteen different organizations around the world doing conservation work to save bees. It’s my dream to actually keep them. I want to be out there caring for them myself, not having staff do it for me. I envy you. It must be an amazing experience, have you done it for long?”

“I put in the hives two years after I bought the land and had the house built, so...eight years now I’ve raised them? If you want, you’re more than welcome to come spend time at the farm. I’ll take you out to the hives and you can see how I care for them. I had special boxes built that are less invasive for collecting the honey. Because of the wildflowers I get the most wonderful honey. My favorite is when they pollinate the lavender. Lavender honey is amazing in tea or on toast.”

“Lavender honey,” Cas’ expression was almost dreamy as he thought about it. “That sounds amazing,” His eyes focused on Dean again and he smiled. “I would  _ love _ to come to your farm. I know you live in Mill Ridge, I’ve listened to my father rant about how he’s unable to find a legal way to obtain it. I even drove through the town a few times. It seems so quaint and wonderful, the kind of place I’d love to live.”

“What do you do? For work, I mean. Do you work for Milton Industries?”

“Technically yes, I’m in charge of the Milton Foods chain. I have no interest in most of the company’s dealings but I’m good at what I do. It will be mine one day, the chain is being willed to me alone. Of course, once father has died I’m tripling the organic foods, gluten free, and dairy free we sell, and I’m launching our own line of those products too, at a more affordable price. I will also be opening a sister store chain in low income areas with affordable, high quality foods. Father comes from a generation where they believe you’re only poor because you’re lazy. If he knew how much money I sink into fixing up low income areas and building affordable housing he’d have a stroke.” Cas’ smirk was full of mischief. 

“How would he feel knowing you’re here talking to me?” Dean asked. Cas smiled and  _ that _ was downright wicked.

“He’d be furious just knowing you’re here but frankly, I don’t care. Anna was right, you’re very nice. Could I interest you in dinner one evening?”

Dean did a silent cheer, though he was careful to temper his excitement. He didn’t want to seem desperate. “I’d like that. What if I made dinner for us at my place? How do you feel about burgers?”

“I love them,” Cas replied. He opened the button on his jacket and moved closer so he could lean his arm across the back of the settee and bring himself closer to Dean. “How about the day after Christmas?”

“That works,” Dean smiled. “Give me your number so I can send you my address and directions once you get to town.”

@@@@@@@@@@@@@@@@@@@@@@

“Anna, darling,” Lenora Milton, wife to Howard Milton the third and mother to Anna and her siblings managed to find her in the growing crowd of party guests and came over to her and the group of people she’d been chatting with. She’d been flirting with a sexy journalist that had been invited to cover the party. Milton parties  _ always _ made it onto the front page of the paper. Of course that was because the Milton’s owned the newspaper. The woman’s name was Charlie and she’d said yes to a date right before Lenora found her. Anna winced at the sound of her mother’s voice, though when she turned around to face her she had a smile ready for the woman.

“Hello, Mother, how are you this evening?” They did the typical cheek air kiss before Lenora looked her over.

“I am well. This is a lovely dress, what label is this?”

“You know, I’m not sure. I bought two similar ones because I wasn’t sure which to wear tonight. This might be the Vera Wang? I wanted something comfortable that I wouldn’t be too warm in. I knew there would be a lot of people here and I would prefer not to sweat my foundation off.” 

“Oh, yes, I had Greta turn the heat down because of that. I think it’s rather comfortable in here. I bought this dress for tonight and it’s a bit warmer than I would prefer,” Lenora touched the sleeve of her dress. They were three quarter, but that wouldn’t have been so bad if she hadn’t chosen a dress with a full, floor length skirt. “It’s a Valentino.” There was that smug tone in her voice that, though it wasn’t actually directed  _ at _ her, it still annoyed Anna very much. She was betting the dress cost no less than four or five thousand. If her mother knew she’d bought the one she had on at Macy’s she’d probably faint.

“Well, you look lovely in it, Mother.” She knew how vain her mother was, and that she wanted praise and compliments, even from her own children. Sometimes she wondered how she and her brothers had survived having two narcissistic parents. Lenora was looking not so subtly around.

“I thought you were bringing a gentleman with you tonight? Where is he?”

Anna saw from the corner of her eye the way Charlie was trying not to smile. She’d told the woman why she’d brought a man as her date. “He went to get a drink, I believe.”

“You’re  _ sure _ you brought a date?” Her mother’s teasing was never  _ just _ teasing. There was the accusation of lying to get out of being set up.

“Yes, Mother,” She tried not to be short with the woman. “I’ll text him. He’s probably talking with someone.” She pulled her phone out and sent Dean a text.

_ Help! My mother found me! Back left corner of the parlor! _

Dean had promised to keep his phone in his inner breast pocket so he’d hear her texts. She just hoped he actually heard it. 

“So tell me about him!” Lenora loved to gossip. It was another thing Anna didn’t like. She was dying to just escape and go home, though she’d have loved to take Charlie with her. 

“Well, he’s a good friend of mine. We go riding quite often,” She took a sadistic sort of pleasure in the way her mother’s smile disappeared.

“Friend?” Lenora asked flatly. “I thought you were seeing him. You’re saying you’re not?”

“Mother,” She gave her sweetest smile. “I brought a date, I never said I was seeing him. Dean is my best friend.”

“Dean?” Charlie blurted, her green eyes going wide. “Dean Winchester?”

Anna looked at her only to see her staring past them at the two men approaching.

“Charlie, what are you doing here?” Dean spotted his friend first and kissed her cheek and smiled.

“I’m covering the party,” She pointed to her cameraman as she held up her pad of paper. “What are you doing here?”

“Yes,  _ what are you doing here? _ ” Lenora demanded. It was clear she knew  _ exactly _ who Dean was. She kept her voice low so the other guests didn’t hear their conversation. Dean seemed not to be put off by her anger. He offered his most charming smile but Cas spoke before he could.

“Anna brought him tonight to introduce him to me. We have a date planned. We’re going riding and we’re going to have a lovely dinner at his house, back in Mill Ridge.” There was Dean’s proof that Anna’s little brother was as rebellious, or more so than she was. It sure would be interesting if something came of dating the man. Downright scandalous, really. That thought made him laugh inside. Cas slid his hand into Dean’s and smiled at his mother. Her look was one of outrage.

“Why? Why do you children insist on doing this to me? Is your goal to humiliate me? To embarrass me?” She hissed. 

“Why does everything have to revolve around you?” Cas didn’t raise his voice, he didn’t even sound angry. “Why do you assume that everything we do is to hurt you? Did it ever dawn on you that we’re just trying to live our lives? Dean is nice, and Anna speaks very highly of him. Just talking to him has been very enjoyable, much more so than I could have hoped for. So I’m going on a date with him, whether you approve or not.”

“Your father-”

“No,” He interrupted her. “You’re not going to try to shame me and scare me with threats of how he’ll be angry with me. I’m gay, I told you that when I was fifteen. It’s not a big deal and I’m not going to embarrass anyone. I may do things to bug you but who I date is not part of that.”

“He’s Dean Winchester!” Lenora hissed, her eyes darting around to see who was close enough to hear their conversation. Her gaze fell on Charlie who jumped at the sheer fury in the woman’s eyes.

“I don’t know why you’d think I care that Dean’s here,” She said. “He’s my best friend but I had no idea he’d be here.”

“He’s not supposed to be here!” Lenora stood up straight and touched her hair, making sure every strand was still perfectly in place. “Howard will hear about this.” She raised her hand, ready to snap her fingers and call the security her children knew was never far.

“Mom, I’m a lesbian.” Anna blurted. Lenora froze, her blue eyes large as saucers and her mouth hanging open. When she fainted he jumped forward to catch her before she hit the floor. Everyone around them stared, and then the rest of the room started whispering, the gossip already starting. God, Dean  _ hated _ snobby rich people.

“Well, that was not surprising.” Cas sighed as he gently.

“Please don’t print that,” Anna rolled her eyes and shook her head. “You might  _ actually _ give her a heart attack.” She shooed away people that were coming to gawk. Nothing like snobs looking for a reason to talk behind their mother’s back. Charlie snapped her fingers in front of her cameraman and shook her head. He lowered the camera.

“I didn’t take any pictures.” He handed the camera over to her and she looked through the pictures to make sure Dean wasn’t in any of them.

“Wouldn’t matter, their parents own the paper,” Dean said. “You really think they’d let that be put in there?” He looked at the people lingering about. “Didn’t you say she wasn’t feeling well?” He asked a bit louder so the people standing around could hear. “She said her dress was making her hot?”

People began murmuring, repeating what Dean was saying and it spread through the room like wildfire.

“Thank you,” Cas whispered. “She’ll be mortified later but you’ve done some damage control. We’ll make sure she knows you were the one to help her.”

“I think we should go,” Anna touched Dean’s arm. “Before our father comes.”

“Alright, if you think that’s best.” He nodded and offered his arm. Dean passed off his empty tumbler and Anna did the same with her champagne flute. He said goodbye to Cas as she said goodbye to Charlie and then he was whisking her out the door, handing over the ticket to the valet.

“That was a rather eventful party,” He commented as they headed away from the Milton mansion. “I’d prefer never to attend one again.”

Anna was busy taking the pins out of her hair but she still chuckled. “That’s the most eventful one I’ve ever attended too. Hopefully my mother goes along with your story about her dress making her too hot. My brothers will make sure of it.”

“Were the rest of them there? I didn’t even see Mike or Luke, I’d have recognized them.”

“They were there, they just prefer to avoid our parents as much as I do. Hell, I found Mike and his wife in the den, sipping champagne and biding the time until they could leave, and Luke and Bart are hiding in the kitchen. I spoke to most of them briefly. Everyone was amused that I’d invited you as my date. Gabe, the brat that he is, invited the heiress to the Cohen grocery empire, then marched right up to our father to introduce her. Dad nearly popped a blood vessel. He’ll know you were there too, I’m sure most of the people there recognized you. You know, tonight might have actually gotten my brothers and I off the mandatory guest list for their parties. I sure hope so,” She scratched at her scalp, sighing with how good it felt to get the five million pins out of her hair. “So you met my brother, Cas. He’s a sweetheart, right? My partner in crime. I know he likes you. He asked you out?”

“No, I asked  _ him _ out. I invited him over to my place. I’m going to take him out to the hives, he wants to see the bees, then we’re going riding. After that I’m making a nice dinner. I’m really looking forward to it. I just wish you’d introduced us sooner.” 

Anna ran her fingers through her hair and looked over at him. “He was seeing someone, a real asshole that we all hated. But he’s single now, so I told him all about my hot, single, billionaire friend that donates millions upon millions to various conservation projects, who keeps bees, recycles, has strong ethics and morals, and bought his entire hometown in order to keep everyone there safe from our father’s clutches. It’s a miracle he didn’t pop a boner right then and there.” Her laughter was full of mischief. He grinned and shook his head.

“But you kept me in the dark that you had a hot, single,  _ gay _ brother that has the same values as me. Shame on you.” He teased.

She giggled and pulled at his ear playfully. “Consider it my Christmas present to you.”

He couldn’t help but laugh. This was why he was one of her best friends. “And you met my friend Charlie. I should have introduced you guys sooner. I’m surprised you didn’t meet at one of the barbecues I host. Sorry about that.”

“Hey, I met her now and she’s great. It’s a very merry Christmas for us both,” She said with a grin. He laughed and nodded.

“A very merry Christmas indeed!”


End file.
